Use of herbicidal benzyl alcohols

ABSTRACT

Substituted benzyl alcohols are applied to the soil to preclude the establishment of weeds in the soil. These compounds are particulate effective in preventing the establishment of crabgrass.

United States Patent [1 1 Lavanish 1 1 USE OF HERBICIDAL BENZYL ALCOHOLS[75] Inventor: Jerome M. Lavanish. Akron. Ohio 173] Assignee: PPGIndustries. Inc.. Pittsburgh. Pa.

[22] Filed: July 25. 1973 [21] Appl. N0.: 382,623

Related US. Application Data [63] Continuation-impart of Scr. No.264.685. June 20.

1972. abandoned.

[52] US. Cl 71/122: 260/592; 260/618 R [51] Int. Cl A0ln 9/24 [58] Fieldof Search 71/122. 124; 260/618 R [56] References Cited UNITED STATESPATENTS 2.806.883 9/1957 Mikcska ct al 260/618 R 2.971.986 2/1961 Nortonct ali 71/122 3,021,371 2/1962 Watson. Jr 71/122 3.375.096 3/1968 Girard71/122 [4 1 Apr. 22, 1975 3/1963 Allais ct a1 71/122 OTHER PUBLICATIONSPrimary E.\'uminer-Glennon H. Hollrah Attorney. Agent, or FirmMark Levin[57] ABSTRACT Substituted benzyl alcohols are applied to the soil topreclude the establishment of weeds in the soil. These compounds areparticulate effective in preventing the establishment of crabgrass.

16 Claims. No Drawings USE OF HERBICIDAL BENZYL ALCOI-IOLSCROSS-REFERENCES TO RELATED APPLICATIONS This application is acontinuation-in-part of my earlier filed application Ser. No. 264.685.filed June 20. 1972 now abandoned. and it is related in its subjectmatter to my earlier filed co-pending applications Ser. Nos. 264,683 nowadandoned and 264.684. also filed June 20. 1972 application Ser. No.382,630 filed even date herewith by applicant claims certain novelcompounds also disclosed in this application.

BACKGROUND OF THE INVENTION 1. Field of the Invention This inventionrelates to the use of chemical compounds of a particular genus asselective pro-emergent herbicides, especially for the control of grassyweeds. and in particular for the control of crabgrass.

2. Description of the Prior Art The prior art does not teach or suggestthat benzyl alcohols of the kind herein disclosed may be used asselective pre-emergent herbicides to control crabgrass.

Norton et al. US. Pat. No. 2,971,986 teaches the compound 4'-isopropyll-methyl benzyl alcohol and the use of the compound as a selectiveherbicide that will kill canary grass but not injure corn or tomatoes.Nothing in this patent suggests that the compound will kill crabgrass,and in fact, tests show that it does not, at rates of up to pounds ofactive ingredient per acre. The compound of the Norton patent differsfrom ones of the instant invention in the fact that the compound ofNorton has only one alkyl group attached to its benzene ring whereas thecompounds of the claims of the instant invention have two to four alkylgroup on their benzene rings.

British Pat. No. 1,039.1 l8 teaches l-trichloromethyl benzyl alcoholswith l to 5 chlorine atoms on the benzene ring. It does not teach pluralalkyl groups on the benzene ring, and it does not teach any activityagainst crabgrass.

In a 1965 abstract (63 CA. 10589), there is a teaching that benzylalcohol enhanced the growth of maize seedlings at low concentrations andinhibited growth at high concentrations, but this does not give anybasis for suspecting any benzyl alcohols of having effectiveness asselective herbicide against crabgrass.

In a 1969 abstract (7l C.A. l2346 w) there is a teaching merely of thepreparation of 2,4,6- triisopropyl-a-methylbenzyl alcohol. but noindication of any use for it.

SUMMARY OF THE INVENTION According to the invention. crabgrass and otherweeds are controlled by applying to soil in the preemergent mode aneffective amount of a compound represented by the formula HCLH | @asmwhere R is hydrogen or C, to C alkyl, each R is independently C to Calkyl; and n is 2. 3 or 4.

Especially good results are obtained in respect to controlling crabgrassin established bluegrass turf by using relatively modest amounts ofl-ethyl-2,4,6- triisopropyl benzyl alcohol. a novel compound.

When R is an alkyl containing from 1 to 4 carbon atoms. it may bemethyl, ethyl, normal propyl, isopropyl, normal butyl. secondary butyl,isobutyl, or tertiary butyl. It is preferred that R be an alkylcontaining from 1 to 3 carbon atoms. Methyl and ethyl are especiallypreferred.

Although each R may contain from 1 to 6 carbon atoms, it is preferredthat each R be independently an alkyl containing from I to 3 carbonatoms. The isopropyl group is especially preferred. The R groups may bethe same or different. It is preferred that all R groups be the same.

Although n may be 2, 3, or 4. values of 2 or 3 are preferred. A valueof3 is especially preferred. The various R groups may be located on anyof the five available places on the ring, but the 2',4-positions, the2,4',5- positions, the 2',4,6'-positions, and the 2',3',5.6'- positionsare preferred. Location in the 2,4,6- positions is especially preferred.

The above classes and subclasses of compounds are especially effectiveagainst annual grasses. particularly small-seeded annual grasses such ascrabgrass. Consequently. crabgrass or other annual grasses may becontrolled by applying to the soil an amount of one or more of thebenzyl alcohols effective to preclude the establishment of crabgrass orother annual grasses in the soil.

Compounds which exemplify the benzyl alcohols which may be usedaccording to the invention are:

2',4'-dimethylbenzyl alcohol 2-methyl-4-ethylbenzyl alcohol2,4'-diisopropylbenzyl alcohol 2'-ethyl-5-amylbenzyl alcohol2,4,5-trimethylbenzyl alcohol 2',4,5'-triisopropylbenzyl alcohol2-6'-dimethyl-3'-propylbenzyl alcohol 2',4',6-trimethylbenzyl alcohol2,4,6'-triethylbenzyl alcohol 2,4,6-triisopropylbenzyl alcohol 2'3,4,6-tetramethylbenzyl alcohol 2,3',5'.6'-tetramethylbenzyl alcohol',6-tetraisopropylbenzyl alcohol ,2 ,3'-trimethylbenzyl alcohol,2-dimethyl-3'-ethylbenzyl alcohol ,2-dimethyl-3'-isopropylbenzylalcohol l,3-dimethyl-2-ethylbenzyl alcoholl-methyl-2'-ethyl-3-amylbenzyl alcohol lmethyl-2'-ethyl-3'-(3-methylbutyl)benzyl alcohol l,2,4-trimethylbenzyl alcohol1,2-dimethyl-4-ethylbenzyl alcohol l-methyl-2-ethyl-4-propylbenzylalcohol l-methyl-2-ethyl-4-(3-methylpentyl)benzyl alcoholl,4'-dimethyl-2-isopropylbenzyl alcoholl-methyl-2'-propyl-4'-ethylbenzyl alcohol 1,2,5-trimethylbenzyl alcoholl.2-dimethyl-5-p ropylbenzyl alcohol l,2-dimethyl-5-isobutylbenzylalcohol l-methyl-2-ethyl-S-amylbenzyl alcohol l-methyl-2 -sec-butyl-5'-isopropylbenzyl alcohol l,2,6'-trimethylbenzyl alcoholl,2-dimethyl-6'-ethylbenzyl alcohol 1.2 '-dimethyl-6'-isopropylbenzylalcohol l-mcthyl-2',6'-diisopropylbenzyl alcohollmethyl-2'-ethyl-6'-isobutylbenzyl alcohol l-methyl-Z '-ethyl-6'-(Z-methylbutyl )benzyl alcohol l3,4'-trimethylbenzyl alcoholl.3-dimethyl-4'-ethylbenzyl alcohol l 3-dimethyl-4'-propylbcnzyl alcoholl4'-dimethyl-3'-ethylbenzyl alcohol lmethyl-3'-ethyl-4-amylbenzylalcohol l-mcthyl-2'-ethyl-4-hexylbenzyl alcohol .3',5'-trimcthylbcnzylalcohol .3'-dimethyl-5-ethylbenzyl alcohol.3'-dimethyl-5-isopropylbenzyl alcohol 3'-dimcthyl-5-tert-butylbenzylalcohol -mcthyl-3',5'-diisopropylbenzyl alcohol.2',3',4'-tctramethylbcnzyl alcohol .2,3'-dimethyl-4ethylbenzyl alcohol,2'.,6'-trimcthyl-4'-tcrt-butylbcnzyl alcohol.4'-dimethyl-2',3-diethylbenzyl alcohol .2',3'.5'-tctramethylbenzylalcohol ,2,3'-trimcthyl-5-isopropylbenzyl alcohol.2'-3'-trimcthyl-5'-butylbenzyl alcohol.2.6'-trimethyl-4-(2,3-dimethylbutyl)benzyl alcohol.3-dimethyl-2'-ethyl-5'-isobutylbcnzyl alcoholl-methyl-2'.3,6'-triisopropylbenzyl alcohol l-methyl-2'-ethyl-3,6'-diisopropylbenzyl alcohol l 6'-dimethyl-2-isopropyl3'-ethylbenzylalcohol l 2',4'.5'-tctramethylbenzyl alcohollmethyl-2',4'.5'-triisopropylbenzyl alcoholl.2'-dimethyl-4',5'-diethylbenzyl alcohol l.2,4-dimethy|--ethylbenzylalcohol l.2',4,6-tetramethylbenzyl alcohollmethyl-2',4',6-triethylbenzyl alcoholl-methyl-2,4',6'-triisopropylbenzyl alcoholl-mcthyl-2'-ethyl-4',6'-diisopropylbenzyl alcoholl-mcthyl-2-isopropyl-4'-isobutyl-6'-ethylbenzyl alcohol l-methyl-2,4'-dipropy|-6'-isopropylbenzyl alcohol l.3',4,5'-tetramethylbenzylalcohol l .2,3 ',4',5'-pentamethylbenzyl alcoholl-methyl-2,3',4',5'-tetraisopropylbenzyl alcoholl.2',3-trimcthyl-4',5'-diethylbenzyl alcoholl,2',4-dimethyl-3-ethyl-5-isopropylbcnzyl alcohol 1,2 l-m,3,4',6'-pentamethylbenzyl alcohol ethyl-2,3,4',6'-tetrapropylbcnzylalcohol l-methyl-2,3',4,6'-tetraisopropylbcnzyl alcoholl-methyl-2'.3,5,6'-tetraisopropylbenzyl alcoholl-ethyl-2',3'-dimethylbenzyl alcohol l,3'-diethyl-2-methylbenzyl alcoholl,2-diethyl-3'-isopropylbcnzyl alcohol l-ethyl-2'-propyl-3'-methylbenzylalcohol l-ethyl-2'-methyl-3'-amylbenzyl alcoholl-ethyl-2,4'-dimethylbenzyl alcohol l-ethyl-2',4-diisopropylbenzylalcohol l.2-dicthyl-4-methylbenzyl alcoholl.2'-diethyl-4-tert-butylbenzyl alcohol l-ethyl-2'-propyl-4-(l-methylbutyl)benzyl alcohol l-ethyl-2',5'-dimethylbenzyl alcoholl.2',5-triethylbenzyl alcohol l-ethyl-2-methyl-5'-isopropylbenzylalcohol l,2-diethyl-5'-(2,2,-dimethylpropyl)benzyl alcoholl-ethyl-2',6-dimethylbenzyl alcohol l,2,6'-triethylbenzyl alcoholl-ethyl-2',6'-diisopropylbenzyl alcohol l-ethyl-2',6-dibutylbenzylalcohol l,6'-diethyl-2'-methylbenzyl alcohol '4l-ethyl-2-methyl-6'-propylbenzyl alcohol l-ethyl-3,4'-dimethylbenzylalcohol l.4'-diethyl-3-methylbenzyl alcohol l.3'-diethyl-4'-methylbenzylalcohol l-ethyl-3,5'-dimethylbenzyl alcoholl-ethyl-3,5-diisopropylbenzyl alcohol l,3'-diethyl-5-tert-butylbenzylalcohol l-ethyl-2,3',4'-trimethylbenzyl alcoholl,4-diethyl-2,3-dimethylbenzyl alcohol l-ethyl-2,3',5'-trimcthylbenzylalcohol 1-ethyl-2,3,5'-triisopropylbenzyl alcoholl,5'-diethyl-2',3'-dimethylbenzyl alcoholl,2-diethyl-3',5'-dibutylbenzyl alcohol l.2',5-triethyl-3'-methylbenzylalcohol l-ethyl-2,5'-dlmethyl-3'-propylbenzyl alcoholl-ethyl-2',3,6'-trimethylbenzyl alcohol l,2,3,6'-tetraethylbenzylalcohol l,2,6'-triethyl-4'-hexylbenzyl alcoholl.2,6-triethyl-3'-methylbenzyl alcohol l,2,6-diethyl-3'methylbenzylalcohol l-ethyl-2',4,5'-trimethylbenzyl alcoholl,2,4',5'-tetraethylbenzyl alcohol l-ethyl-2',4,5'-tripropylbenzylalcohol l-ethyl-2',4,5'-triisopropylbenzyl alcoholl-ethyl-2',4',5'-tributylbenzyl alcoholl-cthyl-2',4',5'-triisobutylbenzyl alcoholl-ethyl-2,4'-dimethyl-5-amylben2yl alcoholl.2'-diethyl-4',5'-dimethylbenzyl alcoholl,4'-diethyl-2,5-dimethylbenzyl alcoholl-ethyl-2',5-dimethyl-4'-propylbenzyl alcohol 7l-ethyl-2',4',6'-trimethylbenzyl alcohol l.2',4,6-tetracthylbenzylalcohol l-ethyl-2',4,6'-tripropylbenzyl alcoholl-ethyl-2',4',6'-triisopropylbenzyl alcohol l-ethyl-2,4,6-tributylbnzylalcohol l-ethyl-2',4,6'-triisobutylbenzyl alcoholl-ethyl-2,4',6'-tri-sec-butylbenzyl alcoholl-ethyl-2',4',6'-tri-tert-butylbenzyl alcoholl-ethyl-2',4',6-triamylbenzyl alcoholl-ethyl-2,4'-dipropyl-6'-methylbenzyl alcohol l6'-diethyl-2',4'-diisopropylbenzyl alcoholl.6-diethyl-2',4"-dimethylbenzyl alcohol l-ethyl-2,6'-dimethyl-4-isopropylbenzyl alcohol1-ethyl-2,6'-dimethyl-4'-sec-butylbenzyl alcohol1,2,6'-triethyl-4'-propylbenzyl alcohol l-ethyl-3,4',5-trimethylbenzylalcohol l,3',4',5'-tetraethylbenzyl alcoholl-ethyl-2',3',4,5'-tetramethylbenzyl alcoholl-ethyl-2',3',4',5-tetraisopropylbenzyl alcohol l-ethyl-2',3',4',5-tetrapropylbenzyl alcohol l.3',4'-triethyl-2,5'-dimethylbenzyl alcoholl-ethyl-2',3',4',6'-tetramethylbenzyl alcoholl,2',3',4',6-pentaethylbenzyl alcohol1-ethyl-2,3,4',6'-tetrapropylbenzyl alcohol l-ethyl-2,3',4',6'-tetraisopropylbenzyl alcohol l-ethyl-2,3,4',6-tetrabutylbenzylalcohol l-ethyl-2',3',4',6'-tetraamylbenzyl alcoholl,3,4-triethyl-2',6'-dimethylbenzyl alcoholl-ethyl-2,3,4'-trimethyl-6'-isopropylbenzyl alcohol1-ethyl-2',3',5',6'-tetramethylbenzyl alcoholl,2',3',5,6-pentaethylbenzyl alcohol l-ethyl-2,3',5,6-tetrapropylbenzylalcohol l-ethyl-2',3',5',6'-tetraisopropylbenzyl alcohol l-ethyl-Z ',3',5 ',6'-tetrabu tylbenzyl alcohol 15 '-diethyl-2',3,6'-trimethylbenzylalcohol l-propyl-2,3'-dimethylbenzyl alcohol 5lpropyl-Z'.4'-diisopropylbenzyl alcoholl-propyl-2'-methyl-5'-ethylbenzyl alcoholl-propyl-2',6'-diisopropylbenzyl alcoholl-propyl-2',4',6'-trimethylbenzyl alcoholl-propyl-2'-ethyl-4',5'-dimethylbenzyl alcoholl-propyl-2',4',6"triisopropylbenzyl alcoholl-isopropyl-2',4'-dirnethylbenzyl alcohol l,2,4-triisopropylbenzylalcohol l-isopropyl-2',4'-dimethylbenzyl alcoholl-isopropyl-3',4-dimethylbenzyl alcohol l-isopropyl-2',4-diethylbenzylalcohol l-isopropyl-2',3,5'-trimethylbenzyl alcohol bl-isopropyl-2',4.6-trimethylbenzyl alcoholl-isopropyl-2',4',6'-triethylbenzyl alcoholl.2',4',6-tetraisopropylbenzyl alcoholl-isopropyl-2',3'-dimethyl-5'-propylbenzyl alcoholl-isopropyl-2,3',5',6'-tetramethylbenzyl alcoholl,2',3',5,6-pentaisopropylbenzyl alcohol l-butyl-2',4-dimethylbenzylalcohol l-butyl-2'.4'-diisopropylbenzyl alcoholl-butyl-2',4',5'-trimethylbenzyl alcohol l-butyl-2',4,6-trimethylbenzylalcohol l-butyl-2,4',6-triisopropylbenzyl alcoholl-butyl-2',4,5'-triisopropylbenzyl alcoholl-butyl-2',3',5',6-tetramethylbenzyl alcoholl-butyl-2',3',5',6'-tetrapropylbenzyl alcohollbutyl-2',3',5',6-tetraisopropylbenzyl alcoholl-sec-butyl-2',4'-dimethylbenzyl alcoholl.3'-di-sec-butyl-5'-methylbenzyl alcoholl-sec-butyl-2',4'-diisopropylbenzyl alcoholl-sec-butyl-2',4,6-triisopropylbenzyl alcoholl-sec-butyl-2,3',5',6-tetraisopropylbenzyl alcoholl-isobutyl-2',4dimethylbenzyl alcohol l-isobutyl-2',5'-dimethylbenzylalcohol l-isobuty|-2-methyl-5'-hexylbenzyl alcoholl-isobutyl-2',6-dimethyl-4'-sec-butylbenzyl alcoholl-isobutyl-2,4',6'-trimethylbenzyl alcohol l-isobutyl2',4,6-triisopropylbenzyl alcoholl-isobutyl-2',5-dimethyl-3'-hexylbenzyl alcohol l-isobutyl-Z ',3 ',5 ',6-tetramethylbenzyl alcohol l-isobutyl-2 ',3 ',5 ',6-tetraisopropylbenzyl alcohol l-tert-butyl-2,4-dimethylbenzyl alcoholl-tert-butyl-2',4'-diisopropylbenzyl alcoholl-tert-butyl-2',4,6-trimethylbenzyl alcoholl-tert-butyl-2',4,6-triisopropylbenzyl alcoholl-tert-butyl-2,3',5',6'4etramethylbenzyl alcoholl-tert-butyl-2',3',5',6'-tetraethylbenzyl alcoholl-tert-butyl-2,3',5',6'-tetraisopropylbenzyl alcohol The benzyl alcoholsmay be prepared by the reduction of the appropriate alkyl aryl ketones.One particularly useful reducing agent for this purpose is lithiumaluminum hydride. The reaction may conveniently be conducted in asolvent.

Many of the alkyl aryl ketones used to prepare the benzyl alcohols areknown to the art. In those instances where the compounds having thedesired substitutions are not available, they may be prepared by any ofthe methods well known in chemistry. One of these is the reaction. inthe presence of aluminum chloride, of a substitued benzene with an acylchloride. Some difficulty has been encountered, however. in preparingthe tert-butyl aryl ketones by this method.

The benzyl alcohols, including the l-tert-butylbenzyl alcohols may beprepared by the reaction of the appropriate aryl Grignard reagent withthe appropriate aldehyde. For example,l-tert-butyl-2,4,6-triisopropylbenzyl alcohol may be prepared byreacting 2,4,6-

6 triisopropylphenyl magnesium bromide with pivaldehyde in the presenceof a diethyl ether solvent.

Illustrative preparations of the benzyl alcohols are shown in ExamplesI-Xlll:

EXAMPLE I 2',4',6'-Triisopropylpropiophenone A 3000-milliliter.three-necked flask was fitted with a mechanical stirrer. additionfunnel, and reflux condenser with drying tube. The flask was cooled inan ice bath and charged with 133.3 grams 1.00 mole) of aluminum chloridein 500 milliliters of carbon tetrachloride Then 102 grams 1.10 mole) ofpropionyl chloride in 500 milliliters carbon tetrachloride was added.The addition funnel was charged with 204 grams 1.00 mole) ofl.3.5-triisopropylbenzene in 300 milliliters of carbon tetrachloride.The funnel solution was added dropwise over 260 minutes at the ice bathtemperature while vigorous stirring was maintained. The yellowgreenslurry was stirred for an additional 120 minutes and then poured into600 grams of ice. After the ice melted the layers were separated and theorganic phase was washed with l000 milliliters of water and then with500 milliliters of 5 percent sodium bicarbonate solution and then driedover anhydrous magnesium sulfate. Removal of the solvent in a rotaryfilm evaporator gave 244.3 grams of crude2',4',6'-triisopropylpropiophenone as moist pale yellow crystals. Thiswas used without further purification. The product may be depicted ashaving the structural formula:

CH CH l-Ethyl-2',4,6'-triisopropylbenzyl Alcohol A 3000-milliliter flaskwas outfitted as previously described. The flask was charged with l9.0grams (0.50 mole) of lithium aluminum hydride in 1000 milliliters of dryether. The addition funnel was charged with the 244.3 grams (0.938 mole)of the previously prepared triisopropylpropiophenone in 400 millilitersof dry ether. The addition was made dropwise at room temperature over350 minutes. Stirring was continued overnight, after which the reactionmixture was heated to reflux for l 10 minutes. After cooling there wasthen added dropwise l9 milliliters of water, l9 milliliters of 15%sodium hydroxide solution, and then 57 milliliters of water. Celitediatomaceous earth was then added to aid in filtering and this slurrywas then suction filtered through a bed of magnesium sulfate. The filtercake was washed with two 100 milliliter portions of ether and solventwas removed from the combined filtrate in a rotary film evaporator togive 237.4 grams of crude l-ethyl-2',4',6'-triisopropylbenzyl alcohol.The crystals were dissolved in 400 milliliters of hot hexane and thenplaced in a freezer to facilitate crystallization. The crystals weresuction filtered and dried at 50C. and 40 millimeters Hg. They weighed202.4 grams and had a melting point range of 98l02.5C. The product maybe depicted as having the structural formula:

titt s-a HCOH (C113) 110 ca(ca 2 CH(CH3)2 EXAMPLE ll 2 ',4 ',6'-Triisopropylpropiophenone A 3000-mil1iliter. four-necked flask wasequipped with a mechanical stirrer. addition funnel. stopper, and refluxcondenser with drying tube. The flask was charged with 147 grams 1.10mole) of aluminum chloride and 500 milliliters of carbon tetrachlorideand cooled in an ice bath. Then 102 grams (1.10 mole) of propionylchloride in 500 milliliters of carbon tetrachloride were added. Theaddition funnel was charged with 204 grams (1.00 mole) of1,3.5-triisopropylbenzone which was added with stirring over a period ofabout 2 hours. The mixture was stirred at ice bath temperature for 3hours and then poured over 1000 grams of crushed ice. The flask wasrinsed with 50 milliliters of carbon tetrachloride and 50 milliliters ofwater which were added to the ice slurry. After the ice had melted thetwo liquid phases were separated and the organic layer was washed with1000 milliliters of water and 500 milliliters of 5% sodium bicarbonatesolution. After drying over magnesium sulfate, the organic phase wasfiltered. Solvent was removed from the filtrate in a rotary filmevaporator at 50C. and 20 millimeters Hg to give 255.6 grams of paleyellow crystals having a melting point range of 81.584C. which were usedwithout further purification. Repetition of the above procedure two moretimes yielded 257.3 grams of crystals having a melting point of 82-84C.and 256.7 grams of crystals having a melting point range of 8384C.

1-Ethyl-2',4.6-triisopropy1benzyl Alcohol A 3000-mil1iliter.three-necked flask was fitted with a mechanical stirrer. additionfunnel, and reflux condenser with drying tube. The flask was chargedwith 9.5 grams (0.25 mole) of lithium aluminum hydride in 1000milliliters of anhydrous ether. The addition funnel was charged with130.2 grams (0.500 mole) of triisopropylpropiophenone in 300 millilitersof dry ether which was added with stirring over a period of about 2hours. The slurry was then heated to reflux for about 2 hours. Aftercooling, 9.5 milliliters of water. 9.5 milliliters of sodium hydroxidesolution. and 28.5 milliliters of water were added dropwise. The slurrywas then suction filtered through a bed of magnesium sulfate. Solventwas removed from the filtrate in a rotary film evaporator at about 50C.and millimeters Hg to give 128.2 grams of white powder. The aboveprocedure was repeated five more times to give the following weights ofproduct: l26.5 grams, 127.2 grams, 127.5 grams, 125.2 grams, and 127.2grams. respectively.

EXAMPLE Ill 1-Ethyl-2,4',6-triisopropylbenzyl Alcohol A 500-milliliter.three-necked flask was equipped with a mechanical stirrer and acontinuous extractor with a reflux condenser equipped with drying tube.The flask was charged with 65.5 grams (0.25 mole) of 2',4-,6'-triisopropylpropiophenone in 250 milliliters of dry ether. Theextractor was charged with 2.9 grams of lithium aluminum hydride. Thecontents of the flask were refluxed with stirring over a period of about9 hours. The extractor was then charged with an additional 2.9 grams oflithium aluminum hydride. The contents of the flask were refluxed withstirring over a period of about 12 hours. The extractor was replacedwith reflux condenser and an addition funnel was affixed to the flask.After cooling by the successive addition of 6 milliliters of water, 6milliliters of 15 percent sodium hydroxide, and 18 milliliters of water,the resulting slurry was then suction filtered through a bed ofmagnesium sulfate. The solvent was removed from the filtrate on a rotaryfilm evaporator to give 57.9 grams of white solid. Recrystallizationfrom normal hexane gave 47.4 grams of crystals having a melting pointrange of 99102C. The product may be depicted as having the structuralformula:

$1 011 acoa (CH HC Gym-RG1 2 CH (CH 2 EXAMPLE 1V1-Methy1-2,4,6'-triisopropy1benzyl Alcohol A 250-milliliter,three-necked flask was equipped with a mechanical stirrer, additionfunnel, and reflux condenser with drying tube. The flask was chargedwith 0.7 gram (0.018 mole) of lithium aluminum hydride in 50 millilitersof dry ether. The addition funnel was charged with 14.7 grams (0.0598mole) of 2,4',6'- triisopropylacetophenone in 50 milliliters of dryether and this solution was added with stirring over a period of about30 minutes. The resulting slurry was then heated to reflux for 1 hour.The excess lithium aluminum hydride was then destroyed by sequentialaddition of 1 milliliter of water. 1 milliliter of 15 percent sodiumhydroxide and 5 milliliters of water. The resulting white slurry wasthen suction filtered through a bed of magnesium sulfate. The solventwas removed from the filtrate on a rotary film evaporator to give 13.4grams of a viscous liquid which crystallized on standing.Recrystallization from normal hexane gave 10.2 grams of crystals havinga melting point range of 8892C. The product may be depicted as havingthe structural for mula:

9 a HCOl-l (CH3)2HC ca(ca c 1(cn EXAMPLE V2',4',6'-Triisopropylbutyrophenone A SOO-milliliter. three-necked flaskequipped with a mechanical stirrer. addition funnel. and refluxcondenser with drying tube was charged with 16.0 grams of aluminumchloride and 100 milliliters of carbon tetrachloride and cooled in anice bath. The flask was charged with 13.9 grams of butyryl chloride and25 milliliters of carbon tetrachloride. The funnel was charged with 20.4grams of l.3.S-triisopropylbenzene and 25 milliliters of carbontetrachloride which were added with stirring over a period of about 75minutes. The slurry was stirred for an additional 30 minutes and thenpoured over 250 grams of crushed ice. After melting the layers wereseparated and the organic phase was washed with two 200 milliliterportions of water and then with 200 milliliters of 5 percent sodiumbicarbonate solution. Drying over magnesium sulfate. filtering. andremoval of solvent under vaccum gave 2',4.6'- triisopropylbutyrophenone(26.0 grams) as a yellow liquid. The product may be depicted as havingthe structural formula:

c (011 H0 M011 2 l-Propyl-2',4',6'-triisopropylbenzyl Alcohol A500-milliliter. three-necked flask was equipped with a mechanicalstirrer, addition funnel, and reflux condenser with drying tube. Theflask was charged with 1.2 gram oflithium aluminum hydride in 100milliliters of dry ether. The addition funnel was charged with 26.0grams of 2,4,6-triisopropylbutyrophenone in 100 milliliters of dryether, and this solution was added with stirring over a period of about70 minutes. The resulting slurry was then heated to reflux for about 200minutes. The excess lithium aluminum hydride was then destroyed bysequential addition of 1.5 milliliters of water. 1.5 milliliters ofpercent sodium hydroxide, and 7 milliliters of water. The resultingslurry was then suction filtered through a bed of magnesium sulfate. Thesolvent was removed from the filtrate on a rotary film evaporator togive 19.8 grams of viscous liquid which crystallized on standing.Recrystallization twice from normal hexane gave 7.3 grams of crystalshaving a melting point range of 99-l02C. The product may be depicted ashaving the structural formula:

10 Cl-l Cl-l Cl-l H OH (CH3) H CH(CH a(cH EXAMPLE v12,4,6-Triisopropylisobutyrophenone A SOO-milliliter flask equipped witha mechanical stirrer. addition funnel. and reflux condenser with dryingtube was charged with 16.0 grams of aluminum chloride and 100milliliters of carbon tetrachloride and cooled in an ice bath. The flaskwas charged with 13.9 grams of isobutyryl chloride and 25 milliliters ofcarbon tetrachloride. The addition funnel was charged with 20.4 grams ofl.3.S-Iriisopropylbenzene which was added over a period of aboutminutes. After stirring for 50 minutes, the slurry was poured over 250grams of crushed ice. On melting. the layers were separated and theorganic phase was washed with two 200- milliliter portions of water andthen with 200 milliliters of 5 percent sodium bicarbonate solution.After drying over magnesium sulfate. filtering. and removal of the otherunder vacuum. there were obtained 30.0 grams of2.4,6-triisopropylisobutyrophenone as a yellow liquid which solidifiedon cooling. The product may be depicted as having the structuralformula:

l,2',4,6'-Tetraisopropylbenzyl Alcohol A 500-milliliter, three-neckedflask was equipped with a mechanical stirrer, addition funnel, andreflux condenser with drying tube. The flask was charged with 1.7 gramsof lithium aluminum hydride in milliliters of dry ether. The additionfunnel was charged with 24.4 grams of2,4',6-triisopropylisobutyrophenone in 100 milliliters of dry ether andthis solution was added with stirring over a period of about 75 minutes.The resulting slurry was then heated to reflux for 2 hours. The excesslithium aluminum hydride was then destroyed by sequential addition of 2milliliters of water. 2 milliliters of 15% sodium hydroxide, and 6milliliters of water. The resulting slurry was then suction filteredthrough a bed of magnesium sulfate. The solvent was removed from thefiltrate on a rotary film evaporator to give 20.7 grams of white solid.Recrystallization from normal hexane gave 16.1 grams of crystals havinga melting point range of 9 l93C. The product may be depicted as havingthe structural formula:

CH(CH3) 2 HOH (on uc 11(011.)

EXAMPLE Vll 2',4',6'-Triisopropylbenzyl Alcohol Into a l-milliliterboiling flask equipped with a reflux condenser were placed 2.6 grams(0.040 mole) of 85% potassium hydroxide pellets. 50 milliliters oftertbutyl alcohol. and 5.0 grams (0.020 mole) of2,4.o-triisopropylbenzyl chloride. After heating to reflux for about 3hours and cooling to room temperature. 200 milliliters of water wereadded and the mixture was extracted with two 50-milliliter portions ofchloroform. The combined extracts were dried over magnesium sulfate andfiltered. Solvent was removed in a rotary film evaporator to give 4.1grams of colorless oil which crystallized on standing. Recrystallizationfrom normal hexane gave 2.4 grams of white crystals having a meltingpoint range of 9293C. The product may be depicted as having thestructural formula:

acoa

H (CH 2 C cu(ca 2 ca (CH3) 2 EXAMPLE VIII 2 .4',6'-Triethylpropiophenone A 500-milliliter, three-necked flask was fittedwith a mechanical stirrer. addition funnel, and reflux condenser withdrying tube. The flask was charged with 20.5 grams (0.154 mole) ofaluminum chloride in 100 milliliters of carbon tetrachloride and thencooled in an ice bath. To this was then added 14.3 grams (0.154 mole) ofpropionyl chloride in 50 milliliters of carbon tetrachloride. Theaddition funnel was charged with 25.0 grams (0.154 mole) of1,3,5-triethylbenzene in milliliters of carbon tetrachloride. Thetriethylbenzene solution was added dropwise over a period of about 2hours with stirring and the resulting red slurry was stirred in the icebath for another period of about 2 hours. The reaction mixture was thenpoured into 300 grams of crushed ice. After the ice had melted, thelayers were separated and the organic layer was washed with twoIOO-milliliter portions of water and then with 200 milliliters of 5%sodium bicarbonate solution. After drying. the carbon tetrachloridesolvent was removed in a rotary film evaporator to give 31.1 grams ofpale yellow liquid. The product may be depicted as having the structuralformula HCH CH CH CH CH l.2',4,6-Tetraethylbenzyl Alcohol A500-milliliter. three-necked flask was fltted with a mechanical stirrer,addition funnel, and reflux condenser with drying tube. The flask wascharged with 2.7 grams of lithium aluminum hydride in 150 milliliters ofdry ether. The funnel was charged with 31.1 grams of2',4,6-triethylpropiophenone and milliliters of dry ether. This wasadded to the flask dropwise at room temperature with stirring over aperiod of about 2 hours. The reaction of mixture was then heated toreflux for 2 hours. After cooling, the reaction mixture was quenched bysuccessive addition of 3 milliliters of water. 3 milliliters of 15%sodium hydroxide solution and 9 milliliters of water. Celitediatomaceous earth filter aid was then added and the slurry suctionfiltered through a bed of magnesium sulfate. The solvent was removedfrom the filtrate in a rotary film evaporator to give 27.4 grams ofcolorless viscous oil. The product may be depicted as having thestructural formula:

(IIHZCH3 H OH CH CH c 1-13 CHZCH3 EXAMPLE Ix2,4'-Diisopropylpropiophenone A IOOO-milliliter, three-necked flaskequipped with a thermometer, mechanical stirrer. and pressure equalizedaddition funnel with drying tube was charged with 43.9 grams of aluminumchloride and 300 milliliters of carbon tetrachloride and cooled in anice bath. Propionyl chloride (32.4 grams) in 50 milliliters of carbontetrachloride was then added. The addition funnel was charged with 50.2grams of 1,3-diisopropylbenzene in 100 milliliters of carbontetrachloride which was added over a period of about 2 hours withstirring. The slurry was then stirred at ice bath temperature for 2hours after which it was poured over 500 grams of crushed ice. After theice melted, the layers were separated and the organic layer was washedwith 200 milliliters of water and 200 milliliters of 5% sodiumbicarbonate solution and then dried over sodium sulfate. Removal ofsolvent under vacuum gave 2',4'-diisopropylpropiophenone (96 grams) as aclear liquid. Distillation through a 10-inch Vigreaux column at0.25-0.41 millimeter Hg gave 53.8 grams of product boiling between96-l00C. The product may be depicted as having the structural formula:

1-Ethyl-2',4'diisopropylbenzy1 Alcohol A 500-milliliter. three-neckedflask was fitted with a mechanical stirrer. addition funnel. and refluxcondenser with drying tube. The flask was charged with 1.9 grams oflithium aluminum hydride in 100 milliliters of dry ether. The funnel wascharged with 21.8 grams of 2',4'-diisopropylpropiophenone and 100milliliters of dry ether. This was added dropwise at room temperaturewith stirring over a period of about 90 minutes. The slurry was thenheated to reflux for 2 hours. After cooling. the reaction mixture wasquenched by successive addition of 2 milliliters of water. 2 millilitersof percent sodium hydroxide. and 6 milliliters of water. Celitediatomaceous earth filter aid was then added and this slurry was suctionfiltered through a bed of magnesium sulfate. Solvent was removed fromthe filtrate in a rotary film evaporator to give 205 grams of acolorless oil. The product may be depicted as having the structuralformula:

CH CH3 CH(CH 2 CH(CH3) 2 EXAM PLE X 1.2,6'-Trimethyl-4'-tert-buty1benzylAlcohol A 500 milliliter. three-necked flask was fitted with amechanical stirrer and a continuous extractor with a reflux condenserequipped with a drying tube. The flask was charged with 5.10 grams of4'-tert-buty1- 2,6-dimethy1acetophen0ne in 250 milliliters of dry ether.The extractor was charged with 2.9 grams oflithium aluminum hydride. Thecontents of the flask were refluxed with stirring over a period of about375 minutes. The extractor was replaced with a reflux condenser and anaddition funnel was affixed to the flask. After cooling, the reactionwas quenched by successive addition of 3 milliliters of water. 3milliliters of 15% sodium hydroxide. and 9 milliliters of water.Magnesol filter aid was then added and this slurry was suction filteredthrough a bed of magnesium sulfate. Solvent was removed from thefiltrate in a rotary film evaporator to give 42.3 grams of whitecrystals having a melting point range of 109-l 12C. The product may bedepicted as having the structural formula:

EXAMPLE Xl 2',4',5'-Triisopropy1propiophenone and2',4,6-Triisopropylpropiophenone A l000-mi1liliter. three-necked flaskwas equipped with a mechanical stirrer. addition funnel. and refluxcondenser with drying tube. The flask was immersed in an ice bath andcharged with 28.0 grams (0.21 mole) of aluminum chloride and 100milliliters of carbon tetrachloride. Propionyl chloride in the amount of20.4 grams (0.22 mole) in 100 milliliters of carbon tetrachloride wasthen added to the flask. The addition funnel was charged with 49.3 grams(0.20 mole of l.2.4.5-tetraisopropylbenzene and 125 milliliters ofcarbon tetrachloride which were added with stirring over a period ofabout 100 minutes. The resulting brick-red slurry was stirred at icebath temperature for 2 hours and then poured over 500 grams of crushedice. After the ice had melted. the layers were separated. The organicphase was washed with 200 milliliters of water and 200 milliliters of 5percent sodium bicarbonate solution and then dried over magnesiumsulfate. Removal of the solvent in a rotary film evaporator gave 50.8grams of viscous yellow oil which partially crystallized on standing.Two recrystallizations from cold normal hexane gave 22.9 grams of whitecrystals having a melting point range of 4762C. Vapor phasechromatographic analysis (5 feet X inch. SE 30 column with 20% by weightloading. 210C., 60 milliliters of helium per minute) showed twocomponents. The first. 2,4,6'-triisopropylpropiophenone. had a retentiontime of 4.8 minutes relative to the air peak and the second component.2',4,5'-triisopropylpropiophenone. had a retention time of 6.1 minutesrelative to the air peak. The peak area ratio of the first component tothe second component was about 1:25. Several hundred milligrams of eachof the above components were collected by preparative vapor phasechromatography using an 8 foot X A inch 10% Carbowax 20 M" column at220C. The 2,4',6-triisopropylpropiophenone sample had a melting pointrange of 588 1C. and the 2',4',5-triisopropylpropiophenone sample had amelting point range of 5169C. The 2',4,6'-triisopropylpropiophenone maybe depicted as having the structure:

(CH ae .@4a(ca 2 CH(CH3) 2 671110311 5 (ca uc CH(CHl-Ethyl-2'.4'.5'-triisopropylbenzyl Alcohol A 50-milliliter.three-necked flask was equipped with a mechanical stirrer. additionfunnel. and reflux condenser with drying tube. The flask was chargedwith 0.07! grams (0.0019 mole) of lithium aluminum hydride in 8milliliters of dry ether. The addition funnel was charged with 0.76grams of 2',4,5'-triisopropylpropiophenone in 8 milliliters of dryether. This was added dropwise over a period of about 5 minutes. Theslurry was then stirred at room temperature for 30 minutes and thenheated to reflux for 150 minutes. After cooling. there were addedsequentially with stirring 70 al of water. 70 [.Li of sodium hydroxidesolution. and 2l0 ul of water. Celite diatomaceous earth filter aid wasthen added. and then reaction mixture was suction filtered through a bedof magnesium sulfate. Removal of solvent in a rotary film evaporatorgave 0.56 of waxy white solid having a melting point range of 6675C. Theproduct may be depicted as having the structural formula:

CH(CH3)2 EXAMPLE Xll A 50-milliliter. three-necked flask was equippedwith a mechanical stirrer. addition funnel. and a reflux condenser withdrying tube. The flask was charged with 0.032 grams (0.00095 mole) orlithium aluminum hydride and 8 milliliters of dry ether. The additionfunnel was charged with 0.32 gram of 2',4',6'-triisopropylpropiophenone(see Example XI) in 8 milliliters of dry ether. This was added dropwiseover a period of about 5 minutes. The slurry was then stirred at roomtemperature for 30 minutes and then heated to reflux for 150 minutes.After cooling. there were added sequentially with stirring 40 pl ofwater. 40 a] of 15 percent sodium hydroxide solution. and I pl of water.Celite diatomaceous earth filter aid was then added. and the reactionmixture was suction filtered through a bed of magnesium sulfate. Removalof solvent in a rotary film evaporator gave 0.22 gram of waxy whitesolid having a melting point range of 7294C. The product may be depictedas having the structural formula:

CH CH H OH EXAMPLE Xlll l-tert-Butyl-2,4,6-triisopropylbenzyl Alcohol Toan ethereal solution of 2,4.6-triisopropylphenyl magnesium bromideprepared by the method of R. C. Fuson and E. C. Homing. Journal oft/1eAmerican Chemical Society. 62. 2962 (1940). is added with stirring amolar equivalent of pivaldehyde. The reaction is then quenched withwater and the organic layer is separated, dried over magnesium sulfate,and filtered. Removal of the ether under vacuum gives a l-tert-butyl-2',4',6-triisopropylbenzyl alcohol. The product may be depicted ashaving the structural formula:

(CH 11C CH(CH One or more benzyl alcohols may be applied to the soil inan amount effective to preclude the establishment of weeds. particularlyannual grasses such as crabgrass, in the soil. The establishmentprecluded is with respect to mature weeds or weeds sufficiently advancedin growth to significantly interfere with the growth of desirableplants; mere germination of weed seeds to product tender seedlings whichare susceptible to attack by the benzyl alcohols is not establishment"as used herein.

The amount of the benzyl alcohol applied to the soil may vary widely.The amount usually is in the range of from 0.1 to pounds per acre.Usually the amount is in the range of 0.1 to 50 pounds per acre or evenin the range of from 0.5 to 20 pounds per acre. Application in the rangeof from 0.5 to 10 pounds per acre is preferred. While these ranges aregenerally applicable, it is recognized that both the optimum and usefulamounts will very depending upon the crop plant involved. if any, theweeds encountered. the particular compound used. the soil condition,cultivation prac-' tices, and the effect desired. The Examples give aneven better indication of the amounts of the benzyl alcohols which mayadvantageously be used when dealing with certain weeds. 1

The benzyl alcohols may be formulated in many ways. Convenientformulations include granular formulations. wettable powders. solutions,and emulsions.

These formulations may be prepared in accordance with the generaltechniques well known to the art. These formulations may be applieddirectly to the soil or they may be diluted before application.

Generally speaking. formulations contain from about 0.1 to 100 percentby weight of the benzyl alcohol. Often formulations contain from about 1to about 50 percent by weight of the benzyl alcohol. Of course. theprecise amount will depend upon such factors as the type of formulationemployed. the type of application. and the mode of application.

Suitable wettable powders typically contain from about I to about 100percent by weight of the benzyl alcohol. Ordinarily wettable powderscontain from l to 85 percent by weight of the benzyl alcohol. The benzylalcohol may be admixed with an inert powder such as silica. chalk. talc.limestone. or clay. Any convenient amount ofdiluent may be used. fromabout to about 90 percent being typical. Small amounts of dispersingand/or wetting agents are usually included in the formulations. Theseusually range from 0.l to 15 percent by weight of the formulation.Ordinarily amounts ranging from 1 to 12 percent are used. The wettablepowder is typically dispersed in water for application.

Solutions of the benzyl alcohol may be prepared. Or-

dinarily concentrated solutions are prepared which. when diluted withwater for application. form emulsions. Solvents suitable for use arenumerous and include many well known for their solvency powers. Examplesinclude the xylenes. toluene. methyl alcohol. ethyl alcohol. isopropylalcohol. the butyl alcohols. water. gasoline. kerosene. diethyl ether.methyl ethyl ether. ethylene glycol. propylene glycol. n-amyl acetate.allyl alcohol. Cello-Solve. methyl acetate, ethyl acetate. acetone.methyl ethyl ketone. methyl isobutyl ketone. benzene. methylnaphthalene. ethyl naphthalene. and edible oils such as corn oil. oliveoil. cod liver oil. cottonseed oil. safflower oil. soybean oil. andpeanut oil.

The formulations of the present invention frequently include smallamounts of various surfactants such as wetting agents. emulsifiers. anddispersants. Anionic surfactants are used for wettable powders.Emulsifiable concentrates generally contain blends of ionic and anionicsurfactants. Many surfactants are available as commercial products. Wellknown dispersing agents which are useful in wcttable powders include thelignin surfactants (ligno sulfonates) such as those described in U.S.Pat. No. 2.49l.832. and the alkaryl sulfonates. The ligno sulfonates ofmost interest are the metallic. notably the sodium and calcium.sulfonate salts. Molecular weights of these materials normally rangefrom about l.000 to about 20.000. Another useful class of surfactantscomprises the formaldehyde-naphthalene sulfonate condensates typified bythose disclosed in U.S. Pat. No. 2.516.095. Other useful dispersingagents are found among the alkali metal derivatives of unsaturatedand-aromati'c hydrocarbons. the alkali metal alcoholates of long chainalcohols. and the anhydrous alkali metal soaps of higher fatty acids.Particularly suitable wetting agents for wettable powders are thetaurates typified by sodium N-methyl-N-oleoyl taurate. Sodium alkylnaphthalene sulfonates and the ,oleic acid ester of sodium isothionateare also especially useful. The condensation products of alkylene oxideswith phenols and organic acids. the polyalkylene derivatives of sorbitanesters. complex ether alcohols. and mahogany soaps are examples ofuseful ionic surfactants. Other surface-active agents of the same orsimilar physical properties are known to the art and can be employed inthe formulations of this invention.

It is often desirable to include in a formulation which is to be mixedwith water a small amount e.g.. about l/l0 to about 1 percent by weightof a suitable antifoaming agent. Useful anti-foaming agents include theditertiary acetylenic glycols. such as those marketed under thetradename SURFYNOL" by Air Reduction Chemical and Carbide Company. 150E. 42nd Street. New York. NY. l00l7. Other compounds known to the art tofunction as anti-foaming agents may be employed if desired. Suchcompounds include 2-octonol. sulfonated oils.and silicones. Usefulsilicones are those of low molecular weight. i.e.. the silicone fluidsor oils. Typical of these are the methyl and ethyl substituted siloxanessuch as the dimethyl siloxanes.

Many of the solvents. solvent systems. and wetting agents are discussedin U.S. Pat. Nos. 2.695.225 and 3.330.642 and Canadian Patent No.85l.658.

The amount of the benzyl alcohol in liquid formulations. including bothsingle-phase solutions and emulsions. is subject to wide variation. Theliquid may contain the benzyl alcohol in very dilute concentrationsalthough it is ordinarily not so dilute that excessive amounts ofsolvent must be applied in order to achieve application of a usefulamount of the benzyl alcohol. The lowest practical concentration formost purposes is the concentration at which the formulation is appliedto the soil. The upper limit of concentration is the solubility limit ofthe benzyl alcohol in the solvent or solvent system used. This will. ofcourse. depend upon the identity of the benzyl alcohol. the identity ofthe solvent system. and the highest temperature for which precipitationof solids is acceptable. It is ordinarily desirable to form aconcentrated liquid formulation. usually an emulsifiable concentrate orconcentrated emulsion. of the benzyl alcohol which will not show precipitation above about 20F. and. more preferably. above about 10F. A broadrange of concentration for the benzyl alcohol in a liquid formulation isfrom 0.05 percent to 90 percent by weight. Liquid concentrates generallycontain from about 10 percent to about 70 percent by weight of thebenzyl alcohol. From about 35 percent to about percent is preferred.Liquid formulations generally contain from about 0.05 percent to aboutpercent of the benzyl alcohol at the time of application. Typically. therange is from 0.1 to 10. From about 0.5 percent to 5 percent ispreferred.

Granular formulations may be prepared by spraying the molten benzylalcohol directly onto an inert carrier. ln another method, a liquidformulation. either a solution or an emulsion. may be applied to theinert carrier particles. Many types of inert carrier particles aresuitable for use in the instant invention. Among these aremontmorillonite. bentonite, vermiculite. corn cobs, and sawdust. Thebenzyl alcohol ordinarily constitutes from about 0.5 to about 50 percentby weight of these granular products. Typically. the benzyl alcoholcontent ranges from about 1 to about 35 percent by weight. From about 10to about 30 percent is preferred.

' In the following examples, test plants are abbreviated according tothe following key:

SUBT Sugar Beet (Bt'm vulgarity L.) CORN Corn (Zea nmyx. L.)

OATS Oats (Arena .rulivu. L.)

CLVR Red Clover (Trifiilium Prlllt'll.\'(. L.) SOYB Soybean (Glycine mm{L} Merr.) COTN Cotton (Gmzv rpium liirxumm. L.) WHT Wheat (Tritium!uvxlirum. L.) PNUT Peanut (Arut'liix Irrpogueu. L.) RICE Rice (Oryzu.rutiru. L.)

KY 86 Kentucky Bluegrass Pun pralvnsis. L.) ALFA Alfalfa (Mt'dit'ugosuliru. L.) FLAX Flax (Linum ul.ti!u1i.\'.\'inmm. L.)

Weeds WOAT Wild Oats (Art'lmfamu, L.)

JMWD Jimsonweed (Damru .nrumunium. L.)

VTLF Vclretleaf (Ahmilun llu'uplirusli. Medic.)

JNGS .lohnsongrass (Sorghum /lUIt'[J('Il.\'('. Pers.)

MSTD Mustard (Bruszricu kuIn-r. L. C. Wheeler. Var. pinuuiifldu. L.

C. Wheeler) Yellow Foxtail (Scmriu glum'u lL.] Beaur.) Barnyard grass(lit'liinm'lilou crusgulli. Beauv.) Crahgrass (Digiluriu .runguinulix[L.| Scop.) Buckwheat (Pu/ 101mm cmn'ulrulm. L.)

Morning Glory (Mixture of lponmt'u purpnrt'a, Roth and Ipumm'al('([(Il!(('ll. .lacq.

Quackgrass (.4grup \'run NIH'ILY {L.| Beauv.) Giant Foxtail (St'luriujilhz'rii. Herrm.)

Green Foxtail (Sc/aria i'iridix [L.] Beaur.)

Purple Nutsedge (Cy-perils rolmulus. L.)

Fall Panicum (Punk-um div/110mmlflurnm. Michx.) Canada Thistle ((irxiumUfl't'llA't lL.] Scop.) Lamhsquarter ((lwnopmlinm ullmm. L.)

SWGS Switchgrass (Punit'nm rirgalum. L.)

ARYE Annual Rycgrass (Lolium muluflnrmn. Lam.)

All plants are groun from seeds unless otherwise indicated:

(R) grown from rhivomcs ('l gm n from tubers YLFX BNGS CBGS BKWT MNGYQKGS GTFX CKBR CTGS GNFX PNSG FPAN (THS LMQR EXAMPLE XIV Test compoundis formulated in a solvent mixture (90% acetone, 8% methanol. and 2%dimethylformamide by volume) to form a solution. Appropriate weedspecies are seeded in individual disposable, threeinch square containerscontaining about 2 inches of soil. A, small amount of sand. usuallyone-eighth to onefourth inch in depth. is applied to cover the seeds.The containers are placed on carrying trays and the carrying trays ofcontainers are then placed on a conveyor belt having a linear speed of1.3 miles per hour. As each tray is moved along on the conveyor belt, ittrips a microswitch which, in turn, activates a solenoid valve andreleases the solution of the test as sprays at the rate of 50 gallonsper acre. The test compounds are immediately watered in and thecontainers then removed to the greenhouse and held for observation.Treatments are observed daily for interim response, final observationsbeing made at the conclusion of the holding period. Any treatmentsinducing especially significant responses are held beyond the regularholding period until such responses can be confirmed. Each result isreported as an Injury Rating which is represented as follows: -novisible effect; 1, 2, or 3-slight injury, a plant usually recovered withlittle or no reduction in top growth; 4, 5, or 6moderate injury, plantsusually recovered but with reduced top growth; 7, 8, or 9severe injury,plants usually did not recover; l0--complete control.

Using this procedure, l'2',6-trimethyl-4-tert-butylbenzyl alcohol wasevaluated. The identities of the test plants, holding periods, rate ofapplication, and results are shown in Table l.

Table I Injury Ratings of Test Plants After Treatment With l.2'.(1'Trimethyl-4'-tert-butylbenlyl Alcohol at It) Pounds Per Acre HoldingPeriod.

The procedure of Example XIV is repeated using 1- ethyl-2', 4',6'-triisopropylbenzyl alcohol as the test compound. The identities ofthe test plants. holding periods, rate of application and results areshown in Table Table 2 lnjury Ratings of Test Plants After TreatmentWith l-Ethyl-2'.4'.6'-triisopropylbenzyl Alcohol at l0 Pounds Per AcreHolding Period Test Plants Days After Application YNSG (T) O 0 WOAT 0 0.IMWD 3 4 VTLF 3 3 JNGS 7 6 PlGW 4 4 MSTD 5 8 YLFX 8 9 BNGS 8 9 C805 9It) BKWT 2 4 MNGY 0 0 EXAMPLE XVI The procedure of Example XIV isrepeated using 1- ethyl-Z, 4, 6'-triisopropylbenzyl alcohol as the testcompound applied at lower rates. The identities of the test plants,holding periods, rates of application, and results are shown in Table 3.

Table 3 lnjur Ratings of Test Plants After Treatment With l-Ethyl-2,4'.6'-triisopropylhenzyl Alcohol Test Holding Period. Days afterApplication Plants 13 20 Rate. pounds per acre 5 2 l 5 2 l YNSG (T) 6 22 5 2 0 WOAT. 2 2 0 2 0 0 JMWD 5 4 2 4 2 0 VTLF 2 0 0 2 0 0 .INGS 8 8 89 8 8 PIGW 5 2 l 4 0 0 MSTD 5 5 3 5 3 2 YLFX 8 8 8 9 8 8 BNGS 8 8 5 9 85 Table 3-Continued Table 5-Continued Injury Ratings of Test PlantsAfter Treatment With l-Ethyl-2'.4.6'-triisopropylbenzyl Alcohol TestHolding Period. Days after Application Plants 13 2t) CBGS II) II) 9 II)II) 9 BKWT (l O (I l) I) (I MNGY (I I) l) (I 0 EXAMPLE XVII Table 4Injury Ratings of Test Plants After Treatment Withl-Ethyl-2'.4'.6-Triisopropylbenzyl Alcohol Test Holding Period. DaysAfter Application Plants 13 27 Rate. pounds per acre 5 2 l 5 2 l CropsSUBT (I (l (I 0 (l CORN (I (I l) (I l) OATS (I (I (I l) I) C LVR 4 3 0 30 U SOYB I) U (l O (J C OTN (l (l l) l) I) WHT 5 5 4 3 Z (l PNL'T 0 I) U(I (I (I RICE (I l) (I U 0 I) KYBG II) l0 l0 l0 9 6 ALFA 5 l (l 0 (l UFLAX l U 0 (l l) (I Weeds QKGS (R) (l (I 0 (I (I O JNGS (R) 4 0 (I (l (I0 JNGS 8 8 (i X 7 I GTFX l4 8 8 9 7 CKBR l0 l0 0 l0 I0 CTGS Z l) (I (I 0U GNFX 9 8 8 9 5 5 PNSG (T) l (I (l O (I 0 FPAN 9 X 8 7 7 6 CTHS (R) (lI) I) (I PIGW 4 4 6 l) t) EXAMPLE XVIII Table 5 Injury Ratings of TestPlants After Treatment With l-Methyl-2'.4'.6'-triisopropylhenzyl Alcoholat l0 Pounds Per Acre Holding Period.

Test Plants Days After Application YNSG (T) (I 0 WOAT 0 0 .IMWD 2 2 VTLF3 4 Injury Ratings of Test Plants After Treatment Withl-Methyl-2'.4'.6'-triisopropylbenzyl Alcohol at 10 Pounds Per AcreHolding Period. Days After Application Test Plants .INGS PIGW MSTD YLFXBNGS CBGS BKWT MNGY EXAMPLE XIX The procedure of Example XIV is repeatedusing I. 2, 4, 6'-tetraisopropylbenzyl alcohol as the test compound. Theidentities of the test plant. holding periods. rate of application, andresults are shown in Table 6.

Table 6 Injury Ratings of Test Plants After Treatment Withl.2.4.6'-TetraisopropyIbenzyl Alcohol at It) Pounds Per Acre HoldingPeriod.

The procedure of Example XIV is repeated using I- propyI-Z, 4',6'-triisopropylbenzyl alcohol as the test compound. The identities ofthe test plants. holding periods. rate of application, and results areshown in Table 7.

Table 7 Injury Ratings of Test Plants After Treatment With l-Propyl-Z .4.6 -triisopropylhenzyl Alcohol at 10 Pounds Per Acre Holding Period.

Test Plants Days After Application YNSG (T) l) 0 WOAT U 0 J MWD 3 0 VTLF4 O .INGS O 2 PIGW 2 2 MSTD 7 9 YLFX 9 9 BNGS 7 4 C 865 9 9 BKWT O MNGYU 0 EXAMPLE XX] Table lO-Continued The procedure of Example XIV isrepeated using I- In ury Ratings of Test Plants 13 Days After Treatmentethyl 4 dnsopropylbenzyl alcohol as the test com withlMama,7.qriisnpmpylbenzyl Alcohol pound. The identities of the testplants. holding period. 5 rate of application. and results are shown inTable 8. Plums Rflleqf Acre] Table 8 C865 9 3 3 BKWT 0 0 0 InjuryRatings of Test Plants l-I Days After Treatment MNGY I) I) 0 WithI-Ethy[-2'.4'-diisopropylhenzyl Alcohol 10 at It) Pounds Per Acre TestPlants Injury Rating EXAMPLE XXIV YNSG (T) I) WOAT 0 l The procedure ofExample XIV IS repeated using 1.24, 6'-tetraisopropylbenzyl alcohol asthe test com- JNQS 0 pound applied at lower rates. The identities of thetest mgr plants. holding period rates of application. results are YLFX 0shown in Table I1. BNGS o (B05 0 Table 11 BKWT U MNGY U Injury Ratingsof Test Plants l3 Days After Treatment Withl.2'.-l.6'-Tetraisopropylhenzyl Alcohol EXAMPLE XX" Test Plants Rate.Pounds Per Acre 5 2 1 The procedure of Example XIV is repeated using 1.2'4. 6'-tetraethylbenzyl alcohol was the test comwag pound. Theidentities of the test plants. holding period. JMWD O O 0 rate ofapplication. and results are shown in Table 9. w VTLF o o u JNGS I) I)(I Table 9 PIGW o o u MSTD 4 I) I) Injury Ratings of Test Plants 14 DaysAfter Treatment j g 1 With I.2.4.6'-Tetraethylhemyl Alcohol BNGS I Q at10 Pounds Per Acre CBCR 9 7 BKWT 0 0 0 Test Plants Injury Rating MNGY I)YNSG (T) o WOAT 0 .IMWD u \'TLF u 4 EXAMPLE XXV .INGS o 0 PIGW I Theprocedure of Example XIV IS repeated using -I- g propyl-Z, 4,6'-triisopropylbenzyl alcohol as the test BNGS 4 compound applied atlower rates. The identities of the g gg test plants, holding periods,rates of application, and MNGY 0 results are shown in Table 12.

Table I2 EXAMPLE XXI" Injury Ratings of Test Plants After Treatment WithThe procedure of Example XIV IS repeated using 1- I Prop) ""wpmpllhenzllAlmhll m hyl-2'. P Py y alcohol as the test Test Plants Holding Period.Days After Application compound applied at lower rates. The identitiesof the 13 20 z ates cation. and retest pl ints holding period ri of appt Rm. pounds sults are shown in Table 10. per acre 5 2 I 5 2 I Table I0Crops Injury Ratings of Test Plants l3 Days After Treatment I$AGT(T) I 88 With I-Methyl-2'.4'.fi' triisopi'opylhenzyl Alcohol JMWD 2 2 0 0 0 0Test Plants Rate. Pounds Per Acre VTLF 3 2 I I) 0 0 5 2 l JNGS l 0 0 a 00 PIGW 2 2 2 0 0 0 YNSG (T) O I) MSTD 4 2 0 4 0 0 WOAT 0 0 .0 YLFX 9 x 49 5 0 .IMWD 0 0 0 BNGS a s 0 5 2 0 VTLF 0 0 0 C805 9 9 5 9 s 5 2 8 BKWT0 o 0 o 0 MSTD 3 0 0 MNGr l 0 0 0 I) 0 YLFX 7 3 3 BNGS 7 5 2 EXAMPLEXXVI The procedure of Example XI\ is repeated using 2'. 4,6-triisopropylbenzyl alcohol on the test compound. The identities of thetest plants. holding periods. rate of application. and results are shownin Table 13.

Table I3 Injury Ratings of Test Plants After Treatment With2'.4'.6'-Triisopropylbenlyl Alcohol at pounds per acre Holding Period.

EXAMPLE XXVlll A soil mixture (2 parts sandy loam. 1 part sand) wasplaced into pots. Pots were then seeded with switchgrass. cheatgrass.yellow foxtail. wild oats. crabgrass. and annual ryegrass. Immediatelyafter planting. the soil surfaces were sprayed with the test compound I-ethyl-2', 4, 6'-triisopropylbenzyl alcohol dissolved in 20 milliliter ofa solvent mixture (90% acetone. 871 methanol. and 271 dimethylformamideby volume). The sprayed pots were placed under light banks and rated 2weeks after application of the test compound.

Test Plants Days After Application 37 The plant injury ratings wereexpressed on a scale rang- YNSG (T) U 0 ing from (no effect) to It)(complete kill). All treat- WOAT u u ments were applied in duplicate.The rates of application and the results are shown in Table I5.

JNGS 5 LMOR 3 MSTD o 0 EXAMPLE XXIX YLFX 6 o BN 3 The procedure ofExample XXVIII IS repeated ex- 8 t: cept that l-ethyl-Z'. 4'.5-triisopropylbenzyl alcohol is MNGY o u used as the test compound. Therates of application and the results are shown in Table 15.

EXAMPLE XXVII The procedure of Example XIV is repeated using a EXAMPLEXXX mixture of l-ethyl-Z. 4', 6-triisopropylbenzyl alcohol The procedureof Example XXVIII is repeated exand l-ethyl-Z'. 4',5'-triisopropylbenzyl alcohol in a 3:2 cept that I-ethyl-Z', 4,6'-triis0propyIbenzyI alcohol molar ratio as the test composition. Theidentities of prepared from a different source is used as the test thetest plants. holding periods. rate of application. and compound. Therates of application and the results are results are shown in Table I4.shown in Table 15.

Table I5 Injury Ratings of Test Plants Two Weeks After Treatment WithVarious Benzyl Alcohols l pound per acre *2. *3. *4. *5.

Test Compound (I 0 (l (l (l (l 8 5 I t) 7 9 (l Table I4 Holding Period.Days After Application Test Plants (l 8 I) 9 3 Ill II) I I) (I YNSG (T)WOAT JMWD VTLF JNGS LMQR MSTD YLFX BNGS (BUS BKW'I" MNGY 2 pounds peracre 5 pounds per acre l) 0 l0 8 I0 7 I0 It) IO 10 It) 10 I0 10 (I It)It) 9 It) It) It) EXAMPLE XXXI Several 3-inch paper pots were filledwith a soil mixture (2 parts clay loam. 1 part sand). Pots were thenseeded with crabgrass. johnsongrass. barnyardgrass. and yellow foxtail.Immediately after seeding. the soil surfaces were sprayed with the testcompound I-ethyl- 2', 4'-diisopropylbenzyl alcohol in 5 milliliters of asolvent mixture percent acetone. 8 percent methanol. and 2 percentdimethylformamide by volume). Each pot received 0.5 milligrams of testcompound for each pound per acre applied. The sprayed pots were wateredsoon after spraying. Plants were grown under light banks with a I2-hourphotoperiod at a temperature of 73i2F. The plants were rated 2 weeksafter application of the test compound. The plant injury ratings wereexpressed on a scale ranging from 0 (no effect) to ID (complete kill).The rate of application and results are shown in Table I6.

Table, 16

Injury Ratings of Test Plants 2 Weeks After Treatment Withl-Ethyl-2.4'-diisopropylhenzyl Alcohol at 50 Pounds Per Acre benzylalcohol at 2 pounds per acre and 5 pounds per acre. respectively.

Three weeks after reseeding of the thinned sods the plots were examinedfor emergence of crabgrass. Ob-

I 5 servations substantiated the previously suggested reason for thelack of crabgrass in the plots, since after CBGS 9 thinning there was asignificant number of crabgrass plants in several of the plots. Becausethe plots had to YLFX 4 be thinned, an artificial condition was createdand only 10 qualitative judgment could be made concerning theperformance of the test compound. In some instances the rotary tillerdug too deeply into the turf, thus expos- EXAMPLE ing untreated soil inwhich crabgrass could be establn the late spring. purchased merionbluegrass (Pm: li h d; r f 11 ju g d I0 be made Whether prawnsis. L.var. Merion) sod was laid down to form 10 15 the crabgrass plants weregrown in a deep hole. an unft. by 3 ft. plots. The sod was allowed tobecome estabtreated soil. or in the shallow rims. lished and 14 daysafter the sod was laid the plots were Plots treated with l-ethyl-2',4'6-triisopropylbenzyl seeded with crabgrass (Digiraria .mnguinalis [L.]alcohol 14 days after laying the sod were judged to Scop.) The seedswere then raked in the grass a d th have less crabgrass than theuntreated seeded control plots sprayed with solutions of l-ethyl-Z', 4,6'-triiso- 30 plots. Of these. plots treated with l-ethyl-2', 4',propylbenzyl alcohol. The sprayer covered a 4-foot 6'-triisopropylbenzylalcohol at 5 pounds per acre and wide strip; therefore. the amount ofcompound sprayed 2 pounds per acre had some crabgrass plants only on onthe plots was calculated based on 40-square-feet the bottom of deepholes cut by the rotary tiller. The plots. Treatments applied to theseeded plots on the plots sprayed with l-ethyl-2', 4,6-triisopropylbenzyl day of seeding were: alcohol 58 days after the sodwas laid were free of crab- 1. Control not seeded with crabgrass, grassat both the 2 pounds per acre and 5 pounds per 2. Control seeded withcrabgrass. acre rates. r 3. l-Ethyl-Z'. 4, 6'-triisopropylbenzyl Alcoholat 5 The hy is pr pyl nzyl 1601101 used pounds per acre. in theseexperiments was dissolved in a solvent mixture 4. l-Ethyl-Z, 4',6'-triisopropylbenzyl Alcohol at 2 0% n 8% methanol, and 2% thy f mpounds per acre. amide by volume) and sprayed on the plots in 140 milli-5. l-Ethyl-Z', 4, 6'-triisopropylbenzyl Alcohol at 1 liters of solvent.each 40-square-feet area receiving pound per acre. 0.415grams/pound/acre of l-ethyl-2', 4, 6'-triisopro- The plots were examinedfor emergence of crabgrass pylbenzyl alcohol. 3 weeks after spraying.None of the plots. treated or unests have been Conducted to compare theresponse treated. contained any crabgrass. The sod was not ofjohnsongrass. crabgrass and other plant species to treated by the sodgrower with any crabgrass herbicide pre'emergent applications of thefollowing: and the sown crabgrass was viable; therefore. only the l.l-ethyl-Z', 4', 6-triisopropylbenzyl alcohol, good quality, condition,and density of the sod pre- B nzyl coho vented the growth of crabgrassin the untreated plots. 40 3. 1-methyl-4'-isopropyl benzyl alcohol andFifty-eight days after laying the sod, the sod plots 4.3,4-dichloro-2-trichloromethylbenzyl alcohol were distressed andseverely damaged by using a rotary The results of ratings after 2 weeksare presented below tiller to decrease turf density. All the previouslytreated in Table 17. As before 0 indicates no injury or control. andsome untreated plots were then reseeded with and 10 indicates a completekill.

Table 17 Rate, pounds Comper acre CBGS ANBG KTBG BNGS RICE .INGS pound(l) l. 9 0 l0 2 O 3 2 l0 4 9 3 0 8 4 l0 8 10 6 l 9 10 10 a 10 9 2 9 (2)l 0 3 4 0 0 0 2 0 3 8* 0 0 0 4 0 0 2 0 0 0 l0 0 0 2 0 0v 0 (3) l 0 0 0 00 0 2 0 0 2 0 0 0 4 0 2 3 0 0 0 l0 0 0 1 0 0 0 (4) l 0 0 1 0 0 0 2 l l l0 0 3 4 2 2 3 2 l 4 l0 5 4 7 3 2 5 Rating anomalous-poor germination.

crabgrass and two previously untreated plots were treated with solutionsof l-ethyl-Z, 4, 6'-triisopropyl- From the foregoing, the superiority ofcompound 1 to other compounds mentioned in the prior art is apparent,particularly with reference to the control of crabgrass.

The especial effectiveness of compound l l-ethyl- 2, 4',6'-triisopropylbenzyl alcohol. as compared with other compounds ofsimilar chemical structure. can be seen from the following Table 18.which summarizes data presented above in the places indicated. In thisTable. compound (1) is compared with the following: (5) l-methyl-Z, 4',6-triisopropylbenzyl alcohol. (6) l-npropyl-Z', 4',6'-triisopropylbenzyl alcohol. and (7) 1. 2'4, 6'-tetraisopropylbenzylalcohol.

The foregoing Table 18 shows an especially better herbicidal effect forthe compound (1) especially at low rates of application on the order ofl or 2 pounds per acre. At rates that low, compound l consistentlyoutperforms compounds 5. 6, and 7. which are (chemically speaking)adjacent homologs.

While I have shown and described herein certain embodiments of myinvention. I intend to cover as well any change or modification thereinthat may be made without departing from its spirit and scope.

I claim:

I. A method for controlling annual grasses comprising applying inpre-emergent mode to soil containing annual grass seeds a compoundrepresented by the structural formula wherein:

R is hydrogen or alkyl containing from I to 4 carbon atoms:

each R is independently an alkyl containing from I to 6 carbon atoms;and

n is 2. 3. or 4; in an amount effective to preclude the establishmentfrom such seeds of annual grass in said soil.

2. The method of claim 1 wherein R is hydrogen or alkyl containing from1 to 3 carbon atoms and each R is independently an alkyl containing from1 to 3 carbon atoms.

3. A method for controlling crabgrass comprising ap plying to soilseeded with crabgrass an amount of a compound represented by thestructural formula H OH wherein:

R is hydrogen or alkyl containing from I to 4 carbon atoms;

each R is independently an alkyl containing from I to 6 carbon atoms:and

n is 2. 3. or 4: effective to preclude the establishment from such seedof crabgrass in said soil.

4. The method of claim 3 wherein each R is isopro- Py 5. The method ofclaim 4 wherein n is 3.

6. The method of claim 5 wherein the isopropyl groups are located in the2, 4', 6'-positions.

7. The method of claim 3 wherein said compound is 2, 4',6-triisopropylbenzyl alcohol.

8. The method of claim 3 wherein said compound is l-methyl-Z'. 4',6'-triisopropylbenzyl alcohol.

9. The method of claim 3 wherein said compound is lethyl-2, 4,6'-triisopropylbenzyl alcohol.

10. The method of claim 3 wherein said compound is l-propyl-Z'. 4',6'-triisopropylbenzyl alcohol.

11. The method of claim 3 wherein said compound is l, 2', 4',6'-tetraisopropylbenzyl alcohol.

12. The method of claim 3 wherein said compound is l-methyl-2',6'-dimethyl-4'-tert-butylbenzyl alcohol.

13. The method of claim 3 wherein said compound is l. 2, 4,6'-tetraethylbenzyl alcohol.

14. The method of claim 3 wherein said compound is l-ethyl-2', 4,5'-triisopropylbenzyl alcohol.

15. The method of claim 3 wherein said compound is l-ethyl-Z',4-diisopropylbenzyl alcohol.

16. The method of claim 3 wherein said crabgrass control is effected inestablished bluegrass turf.

1. A METHOD FOR CONTROLLING ANNUAL GRASSES COMPRISING APPLYING INPRE-EMERGENT MODE TO SOIL CONTAINING ANNUAL GRASS SEEDS A COMPOUNDREPRESENTED BY THE STRUCTURAL FORMULA
 1. A method for controlling annualgrasses comprising applying in pre-emergent mode to soil containingannual grass seeds a compound represented by the structural formula 2.The method of claim 1 wherein R is hydrogen or alkyl containing from 1to 3 carbon atoms and each R'' is independently an alkyl containing from1 to 3 carbon atoms.
 3. A method for controlling crabgrass comprisingapplying to soil seeded with crabgrass an amount of a compoundrepresented by the structural formula
 4. The method of claim 3 whereineach R'' is isopropyl.
 5. The method of claim 4 wherein n is
 3. 6. Themethod of claim 5 wherein the isopropyl groups are located in the246''-positions.
 7. The method of claim 3 wherein said compound is246''-triisopropylbenzyl alcohol.
 8. The method of claim 3 wherein saidcompound is 1-methyl-246''-triisopropylbenzyl alcohol.
 9. The method ofclaim 3 wherein said compound is 1-ethyl-246''-triisopropylbenzylalcohol.
 10. The method of claim 3 wherein said compound is1-propyl-246''-triisopropylbenzyl alcohol.
 11. The method of claim 3wherein said compound is 1, 246''-tetraisopropylbenzyl alcohol.
 12. Themethod of claim 3 wherein said compound is1-methyl-26''-dimethyl-4''-tert-butylbenzyl alcohol.
 13. The method ofclaim 3 wherein said compound is 1, 246''-tetraethylbenzyl alcohol. 14.The method of claim 3 wherein said compound is1-ethyl-245''-triisopropylbenzyl alcohol.
 15. The method of claim 3wherein said compound is 1-ethyl-24''-diisopropylbenzyl alcohol.